Abstract

Photolysis of a series of 2-(trifluoromethyl) quinoline 1-oxides (1a-d) in various solvent is reported. In contrast to the large solvent effects upon the product distribution as found in the photolysis of quinoline 1-oxide and its 2-alkylated derivatives, the photolysis of these four N-oxides shows no such solvent effects and results in the formation of the corresponding 3, 1-benzoxazepines (IIa-d), irrespective of the kinds of solvents used for irradiation. Similarly, the photolysis of 1-(trifluoromethyl) isoquinoline 2-oxide (IV) is also found to give the corresponding 1, 3-benzoxazepine (V) as a sole rearrangement product. A mechanistic rationalization of these photo-rearrangement reactions is presented.

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